Sinapaldehyde

{{Chembox

| ImageFile = Sinapaldehyde.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 244

| ImageName = Kekulé skeletal formula of sinapaldehyde (2E)-2-en with some implicit hydrogens shown and one explicit hydrogen added

| SystematicName = (E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enal{{Cite web|title = AC1L3OEQ - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=119216|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information}}

| OtherNames = {{ubl|

• (trans)-3,5-Dimethoxy-4-hydroxycinnamaldehyde
• Sinapic aldehyde
• Sinapinaldehyde
• Sinapoyl aldehyde
• Sinapyl aldehyde

}}

|Section1={{Chembox Identifiers

| CASNo = 4206-58-0

| CASNo_Comment =

| 3DMet = B00807

| Beilstein = 2215799

| ChemSpiderID = 4444359

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 627-731-3

| KEGG = C05610

| MeSHName = Sinapaldehyde

| ChEBI = 27949

| ChEMBL = 225067

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| PubChem = 5280802

| SMILES = COC1=CC(=CC(=C1O)OC)/C=C/C=O

| StdInChI = 1S/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3/b4-3+

| StdInChIKey = CDICDSOGTRCHMG-ONEGZZNKSA-N

}}

|Section2={{Chembox Properties

| C = 11

| H = 12

| O = 4

| MeltingPtC = 104 to 106

| LogP = 1.686

| pKa = 9.667

| pKb = 4.330

}}

|Section3={{Chembox Hazards

| GHS_ref={{cite web |title=C&L Inventory |url=https://www.echa.europa.eu/web/guest/information-on-chemicals/cl-inventory-database/-/discli/details/160751 |website=www.echa.europa.eu}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|}}

}}

|Section4={{Chembox Related

| OtherFunction_label = alkenals

| OtherFunction = Cinnamaldehyde

Coniferyl aldehyde

DMACA reagent

2-Nitrocinnamaldehyde

}}

}}

Sinapaldehyde is an organic compound with the formula HO(CH₃O)₂C₆H₂CH=CHCHO. It is a derivative of cinnamaldehyde, featuring one hydroxy group and two methoxy groups as substituents. It is an intermediate in the formation of sinapyl alcohol, a lignol that is a major precursor to lignin.Wout Boerjan, John Ralph, Marie Baucher "Lignin Biosynthesis" Annu. Rev. Plant Biol. 2003, vol. 54, pp. 519–46. {{doi|10.1146/annurev.arplant.54.031902.134938}}{{cite journal |doi=10.1105/tpc.010111|title=The Last Step of Syringyl Monolignol Biosynthesis in Angiosperms is Regulated by a Novel Gene Encoding Sinapyl Alcohol Dehydrogenase |year=2001 |last1=Li |first1=Laigeng |last2=Cheng |first2=Xiao Fei |last3=Leshkevich |first3=Jacqueline |last4=Umezawa |first4=Toshiaki |last5=Harding |first5=Scott A. |last6=Chiang |first6=Vincent L. |journal=The Plant Cell |volume=13 |issue=7 |pages=1567–1586 |pmid=11449052 |pmc=139549 |bibcode=2001PlanC..13.1567L }}